3-Pyridinecarboxaldehyde → Ethyl 5-(pyridin-3-yl)-2,4-pentadienoate

HRID 478733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478733
[Li+].CC([N-]C(C)C)C.C(=O)=O.CO.C(OP([CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])(OCC)=O)C.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1>C1COCC1.C(O)(=O)C>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([CH:30]=[CH:22][CH:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:32]=1

Komponenten

7

Edukt 4

HCID 103713-PyridinecarboxaldehydeHCID 2724682Lithium diisopropylamideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 21973728Carbon dioxide methanol

Produkt 1

HCID 73177292Ethyl 5-(pyridin-3-yl)-2,4-pentadienoateAusbeute 89.098,398 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of LDA (16.5 ml of 2M solution, 3.5 g, 0.03 mol) in THF (100 ml) was cooled to −70° C. or below (dry ice-methanol bath) under a nitrogen flow and treated dropwise with ethyl 4-diethylphosphonocrotonate (8.6 g, 0.037 mmol) while stirring. The mixture was further stirred for 15 minutes, treated dropwise with nicotinaldehyde (3.2 g, 0.030 mol), and then stirred at 0° C. for 1.5 hours. Next, the mixture was treated with acetic acid and evaporated. To the residue was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The extract was treated according to conventional techniques. Evaporation of solvent yielded ethyl 5-(pyridin-3-yl)penta-2,4-dienoate as an oil (6.7 g).

Aufarbeitung

  1. stirringThe mixture was further stirred for 15 minutes
  2. stirringstirred at 0° C. for 1.5 hours
  3. customevaporated
  4. additionTo the residue was added saturated aqueous sodium hydrogen carbonate
  5. extractionthe mixture was extracted with ethyl acetate
  6. additionThe extract was treated
  7. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-b1e8fe4b02d94af8afeefda62785ac90
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642250B2

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